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DP you have really great eyes but they are diminished by the facial hair and the fact that you have really, really strong features, nose and brow. Consider some manscaping, some brow waxing and minimizing the full jaw beard to more of a goatee might work IMO.
The burning question is why are you so concerned? Yes, neat and clean is a must but what is driving your original post? Lonely? Looks not working for you? Need a change? Trying to get that one girl to look your way and she seems as far away as Pluto? Be true to thine own self.........
I actually don't mind the long hair on you. I would agree you'd just need to maintain it. Using conditioner and regular trimming every 6-8 weeks sounds about right. Flat iron would be overkill, IMO. A guy's hair can be long and relatively neat, but it doesn't have to be "perfect." Guys shouldn't have to fuss with hair more than most women. Hair can always be tied back for more formal/businesslike occasions. And remember: Our opinions don't really matter. Don't just change it because some people don't like long hair, and you otherwise enjoy the length. You're the one living with it—not us.
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